Acetonitrile → (R)-4-(5-bromo-6-hydroxynaphthalen-2-yl)-4-methyloxazolidin-2-one

HRID 2389136Notes

Reaction equation

HRID 2389136 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH:8]=[C:7]([C@:12]1([CH3:18])[CH2:16][O:15][C:14](=[O:17])[NH:13]1)[CH:6]=[CH:5]2.C(#N)C.[Br:22]N1C(=O)CCC1=O>>[Br:22][C:3]1[C:2]([OH:1])=[CH:11][CH:10]=[C:9]2[C:4]=1[CH:5]=[CH:6][C:7]([C@:12]1([CH3:18])[CH2:16][O:15][C:14](=[O:17])[NH:13]1)=[CH:8]2

Participants

4

Reactant 3

HCID 6342AcetonitrileHCID 67184N-bromobutanimideHCID 51066623(R)-4-(6-hydroxynaphthalen-2-yl)-4-methyloxazolidin-2-one

Product 1

HCID 67413226(R)-4-(5-bromo-6-hydroxynaphthalen-2-yl)-4-methyloxazolidin-2-oneYield 82%

Conditions

Temperature
0 °C

Procedure

(R)-4-(6-Hydroxynaphthalen-2-yl)-4-methyloxazolidin-2-one (Example 4, 5.05 g, 20.8 mmol) was suspended in acetonitrile (50 mL, 1000 mmol) in a capped 200 mL round-bottom flask equipped with a magnetic stir bar. The mixture was cooled to 0° C. and N-bromosuccinimide (3.88 g, 21.8 mmol) was added. The reaction mixture was stirred for 1 hour. HPLC analysis indicated that the reaction was complete. The mixture was filtered. The residue was rinsed with acetonitrile, air dried under vacuum and collected (5.54 g). The crude product required no purification (82% yield).

Workup

  1. customequipped with a magnetic stir bar
  2. filtrationThe mixture was filtered
  3. washThe residue was rinsed with acetonitrile, air
  4. customdried under vacuum
  5. customcollected (5.54 g)
  6. customno purification (82% yield)

Sources & evidence

ORD record
ord-bbef18f5c934492f97d034c8ff239e97
Source dataset
uspto-grants-2012_09
Patent number
US08269043B2

Reaction notes

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